Toluene → 1-((Benzyloxy)carbonyl)-3-methylpiperidine-2-carboxylic acid

HRID 60882

반응식

HRID 60882 반응식
Cl.[CH3:2][CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH:4]1[C:9]([OH:11])=[O:10].Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].C1(C)C=CC=CC=1>[OH-].[Na+].C1COCC1>[CH2:16]([O:15][C:13]([N:5]1[CH2:6][CH2:7][CH2:8][CH:3]([CH3:2])[CH:4]1[C:9]([OH:11])=[O:10])=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

5

반응물 3

HCID 1140TolueneHCID 10387Benzyl chloroformateHCID 696193093-Methylpiperidine-2-carboxylic acid hydrochloride

생성물 1

HCID 666248731-((Benzyloxy)carbonyl)-3-methylpiperidine-2-carboxylic acid

시약·촉매·용매 1

HCID 20445995Sodium hydroxide tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

3-Methylpiperidine-2-carboxylic acid hydrochloride (28.5 g, 31.6 mmol) was dissolved in (1:1) 2 M NaOH/THF (600 mL) and cooled to 0° C. Benzyl chloroformate (31.57 ml, 222 mmol) was then added dropwise and the reaction was stirred overnight. Toluene was then added and organic layer discarded to remove unreacted chloroformate. The aqueous layer was made acidic (pH=2) with conc. HCl and the product was extracted with EtOAc, dried (MgSO4), and concentrated in vacuo to give a crude residue which was used without further purification (41.6 g, 94.5%). 1H NMR (CDCl3, 400 MHz) δ 7.40-7.37 (m, 5H), 5.19 (m, 2H), 4.95-4.72 (m, 1H), 4.14-4.03 (m, 1H), 3.36-3.25 (m, 1H), 1.93-1.53 (m, 5H), 1.20-1.05 (m, 3H).

후처리

  1. customto remove unreacted chloroformate
  2. extractionthe product was extracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0409c044ad724af4a04c943f9ed3440b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440982B2

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